CN1887033B - 含带有1,4-二噻因环的化合物的电荷传输性有机材料 - Google Patents
含带有1,4-二噻因环的化合物的电荷传输性有机材料 Download PDFInfo
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- CN1887033B CN1887033B CN200480035466XA CN200480035466A CN1887033B CN 1887033 B CN1887033 B CN 1887033B CN 200480035466X A CN200480035466X A CN 200480035466XA CN 200480035466 A CN200480035466 A CN 200480035466A CN 1887033 B CN1887033 B CN 1887033B
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 33
- 239000011368 organic material Substances 0.000 title claims abstract description 19
- AKAIWNDBVZJOAJ-UHFFFAOYSA-N 1,4-dithiine Chemical group S1C=CSC=C1 AKAIWNDBVZJOAJ-UHFFFAOYSA-N 0.000 title abstract 3
- 239000002966 varnish Substances 0.000 claims abstract description 35
- 239000002585 base Substances 0.000 claims description 48
- -1 mercapto, carboxyl Chemical group 0.000 claims description 47
- 229930192474 thiophene Natural products 0.000 claims description 46
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 31
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- 229910019142 PO4 Inorganic materials 0.000 claims description 26
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 26
- 239000010452 phosphate Substances 0.000 claims description 26
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 24
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 claims description 22
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- 125000002252 acyl group Chemical group 0.000 claims description 10
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- 238000004519 manufacturing process Methods 0.000 claims description 10
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
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- 239000003960 organic solvent Substances 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
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- UAIZDWNSWGTKFZ-UHFFFAOYSA-L ethylaluminum(2+);dichloride Chemical compound CC[Al](Cl)Cl UAIZDWNSWGTKFZ-UHFFFAOYSA-L 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- WBAPZNLGBRFXDY-UHFFFAOYSA-N oxadiazole;1,3-oxazole Chemical compound C1=COC=N1.C1=CON=N1 WBAPZNLGBRFXDY-UHFFFAOYSA-N 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000002220 fluorenes Chemical class 0.000 claims 1
- OIMWEHOYHJJPJD-UHFFFAOYSA-N pyridine;pyrimidine Chemical compound C1=CC=NC=C1.C1=CN=CN=C1 OIMWEHOYHJJPJD-UHFFFAOYSA-N 0.000 claims 1
- XYVVNRCEUUMOAX-UHFFFAOYSA-N quinoline;quinoxaline Chemical compound N1=CC=CC2=CC=CC=C21.N1=CC=NC2=CC=CC=C21 XYVVNRCEUUMOAX-UHFFFAOYSA-N 0.000 claims 1
- 125000005372 silanol group Chemical group 0.000 claims 1
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- CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 1
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- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
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- 238000002360 preparation method Methods 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- 238000005201 scrubbing Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
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- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
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PCT/JP2004/016095 WO2005043962A1 (fr) | 2003-10-31 | 2004-10-29 | Materiau organique de transport de charge contenant un compose qui possede un cycle 1,4-dithiine |
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KR101064529B1 (ko) * | 2002-11-07 | 2011-09-14 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하수송성 니스 |
US9251923B2 (en) * | 2004-04-30 | 2016-02-02 | Nissan Chemical Industries, Ltd. | Varnish containing good solvent and poor solvent |
EP1950816A4 (fr) * | 2005-10-28 | 2012-02-22 | Nissan Chemical Ind Ltd | Vernis a transport de charge pour procede de pulverisation ou de jet d'encre |
CN101489991B (zh) | 2006-07-18 | 2013-11-06 | 日产化学工业株式会社 | 电荷传输性清漆 |
CN100479228C (zh) * | 2006-08-08 | 2009-04-15 | 中国科学院化学研究所 | 基于电子受体材料的蓝光有机发光二极管的制备方法 |
KR101473294B1 (ko) | 2006-09-13 | 2014-12-16 | 닛산 가가쿠 고교 가부시키 가이샤 | 올리고아닐린 화합물 및 그 이용 |
KR101557109B1 (ko) | 2007-04-12 | 2015-10-02 | 닛산 가가쿠 고교 가부시키 가이샤 | 올리고아닐린 화합물 |
KR20090082778A (ko) | 2008-01-28 | 2009-07-31 | 삼성모바일디스플레이주식회사 | 유기전계발광소자 및 그 제조방법 |
JP5672681B2 (ja) * | 2008-09-18 | 2015-02-18 | 三菱化学株式会社 | 電荷輸送膜用組成物、有機電界発光素子、有機elディスプレイ及び有機el照明 |
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KR20160088440A (ko) | 2008-11-19 | 2016-07-25 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하수송성 재료 및 전하수송성 바니시 |
JP5375434B2 (ja) * | 2009-08-21 | 2013-12-25 | 富士ゼロックス株式会社 | 有機電界発光素子及び表示媒体 |
WO2011091607A1 (fr) | 2010-01-30 | 2011-08-04 | 海洋王照明科技股份有限公司 | Copolymère à motif fluorénylporphyrine-anthracène, son procédé de préparation et son utilisation |
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CN102329415B (zh) * | 2010-07-13 | 2013-04-17 | 海洋王照明科技股份有限公司 | 含咔唑卟啉-喹喔啉共聚物及其制备方法和应用 |
US9431621B2 (en) | 2012-03-13 | 2016-08-30 | The Regents Of The University Of Michigan | Metal oxide charge transport material doped with organic molecules |
JP6098042B2 (ja) * | 2012-04-24 | 2017-03-22 | 日立化成株式会社 | 色変化防止剤、該色変化防止剤を含むインク組成物、該インク組成物を用いて形成した有機薄膜、有機エレクトロニクス素子、有機エレクトロルミネセンス素子、表示素子、照明装置、及び表示装置 |
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WO2016148184A1 (fr) | 2015-03-17 | 2016-09-22 | 日産化学工業株式会社 | Composition de formation de couche de collecte de trous d'élément de photocapteur, et élément de photocapteur |
KR102153447B1 (ko) * | 2015-12-01 | 2020-09-08 | 엘티소재주식회사 | 헤테로고리 화합물 및 이를 이용한 유기 발광 소자 |
WO2017135117A1 (fr) | 2016-02-03 | 2017-08-10 | 日産化学工業株式会社 | Vernis de transport de charges |
JP6717372B2 (ja) | 2016-03-03 | 2020-07-01 | 日産化学株式会社 | 電荷輸送性ワニス |
US20190084920A1 (en) | 2016-03-24 | 2019-03-21 | Nissan Chemical Corporation | Arylamine derivative and use thereof |
JP6443587B2 (ja) | 2016-06-16 | 2018-12-26 | 日産化学株式会社 | スルホン酸エステル化合物及びその利用 |
CN109415310B (zh) | 2016-06-16 | 2022-03-01 | 日产化学株式会社 | 磺酸酯化合物及其利用 |
KR102528211B1 (ko) | 2017-02-07 | 2023-05-03 | 닛산 가가쿠 가부시키가이샤 | 전하 수송성 바니시 |
EP3608983A4 (fr) | 2017-04-05 | 2021-01-13 | Nissan Chemical Corporation | Vernis de transport de charge |
WO2018216507A1 (fr) | 2017-05-25 | 2018-11-29 | 日産化学株式会社 | Procédé de fabrication de film mince de transport de charge |
TWI801471B (zh) | 2017-12-20 | 2023-05-11 | 日商日產化學股份有限公司 | 磺酸酯化合物及其利用 |
JP6958637B2 (ja) | 2017-12-20 | 2021-11-02 | 日産化学株式会社 | 電荷輸送性ワニス及び電荷輸送性薄膜 |
CN112771995B (zh) | 2018-09-25 | 2024-08-16 | 日产化学株式会社 | 带有有机功能膜的基板的制造方法 |
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JPS5649304A (en) * | 1979-09-29 | 1981-05-02 | Hodogaya Chem Co Ltd | Expellent against soil injurious organism |
JPS61152677A (ja) * | 1984-12-26 | 1986-07-11 | Seitetsu Kagaku Co Ltd | 2−ハロアセチルチオフエン類の製造法 |
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JP4868099B2 (ja) * | 2000-11-09 | 2012-02-01 | 日産化学工業株式会社 | 電界発光素子 |
KR101064529B1 (ko) * | 2002-11-07 | 2011-09-14 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하수송성 니스 |
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2004
- 2004-10-29 CN CN201010168167A patent/CN101817810A/zh active Pending
- 2004-10-29 CN CN200480035466XA patent/CN1887033B/zh active Active
- 2004-10-29 TW TW093132998A patent/TW200519184A/zh unknown
- 2004-10-29 US US10/577,438 patent/US7795452B2/en not_active Expired - Fee Related
- 2004-10-29 JP JP2005515167A patent/JP4811573B2/ja not_active Expired - Fee Related
- 2004-10-29 WO PCT/JP2004/016095 patent/WO2005043962A1/fr active Application Filing
- 2004-10-29 KR KR1020067007845A patent/KR101150743B1/ko active IP Right Grant
- 2004-10-29 EP EP04793203.3A patent/EP1691586B1/fr not_active Ceased
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US4319033A (en) * | 1980-12-02 | 1982-03-09 | Uniroyal Ltd. | Method of making certain 2,3-dihydro-1,4-dithiins |
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Juzo Nakayama et al.PREPARATION OF α-QUATER-, AND α-SEPTITHIOP.HETEROCYCLES26 4.1987,26(4),1-3. * |
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Also Published As
Publication number | Publication date |
---|---|
CN101817810A (zh) | 2010-09-01 |
JP4811573B2 (ja) | 2011-11-09 |
EP1691586B1 (fr) | 2015-10-14 |
EP1691586A4 (fr) | 2009-07-01 |
US20070043222A1 (en) | 2007-02-22 |
EP1691586A1 (fr) | 2006-08-16 |
WO2005043962A1 (fr) | 2005-05-12 |
US7795452B2 (en) | 2010-09-14 |
JPWO2005043962A1 (ja) | 2007-05-17 |
CN1887033A (zh) | 2006-12-27 |
KR20060096057A (ko) | 2006-09-05 |
KR101150743B1 (ko) | 2012-06-08 |
TWI355411B (fr) | 2012-01-01 |
TW200519184A (en) | 2005-06-16 |
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